189079-75-2Relevant articles and documents
Synthesis of Pyrrolidines by a Csp3-Csp3/Csp3-N Transition-Metal-Free Domino Reaction of Boronic Acids with γ-Azido-N-Tosylhydrazones
Florentino, Lucía,López, Lucía,Barroso, Raquel,Cabal, María-Paz,Valdés, Carlos
, p. 1273 - 1280 (2021)
The reaction between γ-azido-N-tosylhydrazones and boronic acids leads to the obtention of 2,2-disubstituted pyrrolidines in a domino process that includes 1) diazoalkane formation, 2) intermolecular carboborylation of the diazocompound, and 3) intramolecular carborylation of the azide, and comprises the formation of a Csp3?Csp3 and a Csp3?N bonds on the same carbon atom. The reaction proceeds without the need of any transition-metal catalyst under microwave activation and features wide scope in both reaction partners. It can be applied to both alkyl and arylboronic acids with equal efficiency. With N-tosylhydrazones derived from 2-(2-azidoethyl)-cyclopentanone and cyclohexanone the reactions are highly diastereoselective leading to the cis-fused bicyclic systems as unique diastereoisomers. The scope of the process is illustrated by over sixty examples, including scaffolds present in natural alkaloids, and the mechanistic proposal is suppported by DFT-based computations.
Manganese-catalyzed oxidative azidation of cyclobutanols: Regiospecific synthesis of alkyl azides by C-C bond cleavage
Ren, Rongguo,Zhao, Huijun,Huan, Leitao,Zhu, Chen
supporting information, p. 12692 - 12696 (2015/10/28)
A novel, manganese-catalyzed oxidative azidation of cyclobutanols is described. A wide range of primary, secondary, and tertiary alkyl azides were generated in synthetically useful yields and exclusive regioselectivity. Aside from linear alkyl azides, oth
Azido carbonyl compounds as DNA cleaving agents
Chowdhury, Nilanjana,Dutta, Sansa,Karthick,Anoop, Anakuthil,Dasgupta, Swagata,Pradeep Singh
, p. 25 - 34 (2012/11/07)
Irradiation of azido carbonyl compounds using UV light (≥310 nm) produced triplet alkyl nitrenes and aroyl radicals, which resulted in efficient cleavage of single strand DNA at pH 7.0. DNA cleaving ability of azido carbonyl compounds was found to be dependent on its concentration and substituents on its aromatic ring. Further, newly synthesized naphthalene based azido carbonyl compounds showed DNA cleavage ability at longer wavelength of UV light (≥350 nm) and also binding studies revealed that they bind to ct-DNA by weak intercalation mode.
Pyrazole-based sulfonamide and sulfamides as potent inhibitors of mammalian 15-lipoxygenase
Ngu, Khehyong,Weinstein, David S.,Liu, Wen,Langevine, Charles,Combs, Donald W.,Zhuang, Shaobin,Chen, Xing,Madsen, Cort S.,Harper, Timothy W.,Ahmad, Saleem,Robl, Jeffrey A.
scheme or table, p. 4141 - 4145 (2011/08/06)
A series of inhibitors of mammalian 15-lipoxygenase (15-LO) based on a 3,4,5-tri-substituted pyrazole scaffold is described. Replacement of a sulfonamide functionality in the lead series with a sulfamide group resulted in improved physicochemical properties generating analogs with enhanced inhibition in cell-based and whole blood assays.
Discovery of selective imidazole-based inhibitors of mammalian 15-lipoxygenase: Highly potent against human enzyme within a cellular environment
Weinstein, David S.,Liu, Wen,Ngu, Khehyong,Langevine, Charles,Combs, Donald W.,Zhuang, Shaobin,Chen, Cindy,Madsen, Cort S.,Harper, Timothy W.,Robl, Jeffrey A.
, p. 5115 - 5120 (2008/12/20)
A series of 2,4,5-tri-substituted imidazoles has proven to be highly potent in inhibiting mammalian 15-lipoxygenase (15-LO) with excellent selectivity over human isozymes 5- and P-12-LO. Non-symmetrical sulfamides (e.g., 21a-n) were found to be suitable r
Inhibitors of 15-lipoxygenase
-
Page/Page column 12-13, (2008/06/13)
The present invention provides oxazolyl and thiazolyl inhibitors of 15-LO, pharmaceutical compositions containing such inhibitors and methods for treating diseases related to the 15-LO cascade using such compounds and compositions.
Imidazolyl inhibitors of 15-lipoxygenase
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Page/Page column 14, (2010/02/11)
The present invention provides imidazolyl inhibitors of 15-LO, pharmaceutical compositions containing such inhibitors and methods for treating diseases related to the 15-LO cascade using such compounds and compositions.
A simple and fast procedure for efficient synthesis of β- and γ-azidoarylketones
Singh, Pradeep N. D.,Muthukrishnan, Sivaramakrishnan,Murthy, Rajesh S.,Klima, Rodney F.,Mandel, Sarah M.,Hawk, Michael,Yarbrough, Nina,Gudmundsdottir, Anna D.
, p. 9169 - 9172 (2007/10/03)
A simple and efficient method for preparing β- and γ-azido substituted arylketones has been achieved by short microwave irradiation of the corresponding halo arylketones and sodium azide in DMSO.
Synthesis of 3-halopyrroles
De Kimpe, Norbert,Tehrani, Kourosch Abbaspour,Stevens, Christian,De Cooman, Paul
, p. 3693 - 3706 (2007/10/03)
3-Chloro- and 3-bromo-2-arylpyrroles, which are potential physiologically active compounds in agrochemistry and pharmaceutical sciences, were efficiently prepared from the corresponding 2-aryl-1-pyrrolines by α,α-dihalogenation with N-halosuccinimides and
